19853-10-2

Basic information

• Product Name: 2-BIPHENYLACETONITRILE
• Synonyms: 2-BIPHENYLACETONITRILE;2-([1,1'-Biphenyl]-2-yl)acetonitrile
• CAS NO: 19853-10-2
• Molecular Formula: C₁₄H₁₁N
• Molecular Weight: 193.24
• Mol File: 19853-10-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 122°C 1mm
• Flash Point: 198 °C
• Appearance: /
• Density: 1,07 g/cm3
• Vapor Pressure: 1.27E-05mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-BIPHENYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BIPHENYLACETONITRILE(19853-10-2)
• EPA Substance Registry System: 2-BIPHENYLACETONITRILE(19853-10-2)

Safety Data

• Hazard Codes: Xi,T
• HazardClass: IRRITANT, TOXIC
• Hazardous Substances Data: 19853-10-2(Hazardous Substances Data)

Usage

General Description

2-BIPHENYLACETONITRILE, also known as diphenylacetonitrile, is a chemical compound with the molecular formula C14H11N. It is a colorless, solid compound that is commonly used as a building block in the synthesis of various organic compounds. 2-BIPHENYLACETONITRILE is often utilized in the production of pharmaceuticals, agrochemicals, and other fine chemicals due to its reactivity and versatility in chemical reactions. It has a wide range of applications, including as an intermediate in the synthesis of dyes, perfumes, and other specialty chemicals. Additionally, it is used as a reagent in organic synthesis and can also act as a ligand in coordination chemistry. Overall, 2-BIPHENYLACETONITRILE is a valuable chemical with diverse uses in the field of organic chemistry.

InChI:InChI=1/C14H11N/c15-11-10-13-8-4-5-9-14(13)12-6-2-1-3-7-12/h1-9H,10H2

Upstream product

• 82979-53-1 2-(2,2-difluorovinyl)-1,1'-biphenyl 
• 19853-09-9 2-phenylbenzyl bromide 
• 103-81-1 Benzeneacetamide 
• 1226855-77-1 2-biphenyl-2-ylacetamide 
• 17763-65-4 biphenyl-2-yl trifluoromethanesulfonate 
• 1071-36-9 sodium cyanoacetate 
• 2856-63-5 2-Chlorophenylacetonitrile 
• 224311-51-7 johnphos 
• 75-05-8 acetonitrile 
• 98-80-6 phenylboronic acid 
• 1924-77-2 2-phenylbenzylamine 
• 2928-43-0 2-biphenylmethanol 
• 24973-49-7 biphenyl-2-carbonitrile 

Downstream Products

• 14676-52-9 biphenylacetic acid 
• 1429027-31-5 6-(biphenyl-2-ylmethyl)-[1_.2,4]triazolo[4,3-b]pyridazin-3(2H)-one 
• 1429027-30-4 6-(biphenyl-2-ylmethyl)-pyridazin-3(2H)-one 
• 1429024-66-7 6-(biphenyl-2-ylmethyl)-3-chloro-[1,2,4]triazolo[4,3-b]pyridazine 
• 947-73-9 9-Aminophenanthrene 
• 855926-80-6 2-biphenyl-2-yl-3-oxo-3-phenyl-propionitrile 
• 844-20-2 9-phenylphenanthrene 

Relevant articles and documents

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Structure-Activity Relationship Studies of Pyrimidine-4-Carboxamides as Inhibitors of N-Acylphosphatidylethanolamine Phospholipase D

N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the main enzyme responsible for the biosynthesis of N-acylethanolamines (NAEs), a family of bioactive lipid mediators. Previously, we reported N-(cyclopropylmethyl)-6-((S)-3-hydroxypyrrolidin-1-yl)-2-((S)-3-phenylpiperidin-1-yl)pyrimidine-4-carboxamide (1, LEI-401) as the first potent and selective NAPE-PLD inhibitor that decreased NAEs in the brains of freely moving mice and modulated emotional behavior [ Mock et al. Nat Chem. Biol., 2020, 16, 667-675 ]. Here, we describe the structure-activity relationship (SAR) of a library of pyrimidine-4-carboxamides as inhibitors of NAPE-PLD that led to the identification of LEI-401. A high-throughput screening hit was modified at three different substituents to optimize its potency and lipophilicity. Conformational restriction of an N-methylphenethylamine group by replacement with an (S)-3-phenylpiperidine increased the inhibitory potency 3-fold. Exchange of a morpholine substituent for an (S)-3-hydroxypyrrolidine reduced the lipophilicity and further increased activity by 10-fold, affording LEI-401 as a nanomolar potent inhibitor with drug-like properties. LEI-401 is a suitable pharmacological tool compound to investigate NAPE-PLD function in vitro and in vivo.

Primary Amide Directed Regioselective ortho-C-H-Arylation of (Aryl)Acetamides

An efficient and regioselective palladium(II)-catalyzed primary acetamide assisted ortho arylation of arylacetamide has been discovered. This is the first report where functionalizable primary acetamide (?CH2CONH2) is used as a directing group for C(sp2)-H activation/cross-coupling reactions, circumventing the extra steps of installation and subsequent removal of the directing groups. The synthetic utility of this transformation is demonstrated through the scale-up synthesis. In addition, the primary acetamide can be manipulated into synthetically important derivatives such as nitriles and carboxylic acids.